Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:59 UTC |
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Update date | 2019-11-26 03:12:01 UTC |
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Primary ID | FDB015672 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Bilobalide A |
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Description | Bilobalide A belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure. Bilobalide A is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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CAS Number | 33570-04-6 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C15H18O8 |
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IUPAC name | (1S,4R,7S,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0¹,¹¹.0⁴,⁸]tetradecane-2,6,13-trione |
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InChI Identifier | InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8+,11-,13-,14+,15+/m0/s1 |
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InChI Key | MOLPUWBMSBJXER-NRSGSQFTSA-N |
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Isomeric SMILES | [H][C@]12C[C@@](O)(C(C)(C)C)[C@]34[C@H](O)C(=O)O[C@@]3([H])OC(=O)[C@]14CC(=O)O2 |
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Average Molecular Weight | 326.2986 |
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Monoisotopic Molecular Weight | 326.100167552 |
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Classification |
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Description | Belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene lactones |
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Direct Parent | Ginkgolides and bilobalides |
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Alternative Parents | |
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Substituents | - Bilobalide
- Diterpenoid
- Tricarboxylic acid or derivatives
- Furofuran
- Acylal
- Gamma butyrolactone
- Cyclic alcohol
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Alcohol
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Bilobalide A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-056r-7090000000-409b29d29f5d92b036e1 | Spectrum | Predicted GC-MS | Bilobalide A, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-06dr-9025400000-db65ccd917ab30b1e85a | Spectrum | Predicted GC-MS | Bilobalide A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a6r-0039000000-fd571dbea940514eb044 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a7i-1096000000-473f19a2a3e09916098b | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014r-3091000000-c7c1e8b2c82cbd9fa2db | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0059-0089000000-7e83fcc43328f0da5170 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-0097000000-41ff44d74a98fc8c733b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000l-3190000000-cc31694b1766c38571fa | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0009000000-860df1894ebe815b95f4 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-2039000000-09a3e28dac6072fa36c4 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-1190000000-ea4455a1fec72fb52745 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0009000000-0de6306d29da47cbad7b | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-056r-0039000000-e3b3433b12e8c877e6be | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-9020000000-72a7050fc022305ce16d | 2021-09-23 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 475104 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C07605 |
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Pubchem Compound ID | 545839 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB36735 |
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CRC / DFC (Dictionary of Food Compounds) ID | KFT43-S:KFT43-S |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | C00011512 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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